Cheshire Academy Convocation: New Students, New Mascot Name, New Year
New traditions, speeches, songs, and a name for the Cheshire Academy Cat mark annual ceremony on Simosa Field Cheshire Academy opened its 2026-27 academic year on Monday, September 7, with a lively Convocation, featuring songs and speeches from students, and the unveiling of the school mascot’s forever name. A large crowd of family, friends, and alumni attended the event under picture-perfect skies. The 233-year-old school, […]
10 New Faculty Join Cheshire Academy for 2026-27
Each brings a wealth of experience and talent to academics and student support services Cheshire Academy welcomed 10 new faculty members for the 2026-27 academic year, including classroom teachers and student-facing professionals in College Counseling, Campus Life, and the Roxbury Center for Learning & Leadership. “Cheshire Academy continues to attract talented and experienced faculty and staff and I’m looking forward to working with each of […]
From Cheshire Academy Postgrad to West Point and Beyond
By Ben Vasta PG’16 Starting at Cheshire Academy, I’m grateful for all the connections I made with instructors, staff, and students in one short year that I still stay in contact with today. At CA, I learned the value of consistency. Consistent effort in all things compounds into many great things. Whether that’s studying or […]
IB Extended Essay: A Teacher-Student Collaboration
As you likely have read elsewhere, we hosted Yanying “Nicole” Hao ’21 on April 2, 2026, as our third Alumni in the Classroom visitor. It was an exciting and productive visit focused on her many interests and talents. I want to share a personal story about her that gives even more evidence of her intellectual […]
Finding the Perfect ‘Right-Fit’ College
At Cheshire Academy, personalized college counseling from year one is key. In June, 111 students graduated from Cheshire Academy. The list of colleges they went off to was almost as long as their procession, including nearly 80 institutions from Ivies to “Big 10s” to international business heavyweights like Hult International Business School and IEU—Madrid. When Cheshire Academy […]
Meet Cheshire Academy’s New Varsity Head Coaches
Brian Looney, Bradley Orban, Chris Russo, Kevin Warnock bring decades of collegiate, professional and club-level experience to Cheshire Academy’s athletics program. CHESHIRE, Conn.— Cheshire Academy has announced the appointment of four new varsity head coaches to lead the Cats for the 2026-27 year: Brian Looney, baseball; Bradley Orban, boys’ tennis; Chris Russo, girls’ soccer; and Kevin […]
Cheshire Academy’s Chase Harding Brings Tennis Clinic to Jamaica — NEPSAC Magazine
Recent grad is living CA’s mission of “Individual Growth. Global Purpose.” Tennis player Chase Harding ’26 brought donated rackets and equipment to his hometown of Kingston, Jamaica, because he wanted to host a tennis clinic for kids and foster a love for the sport that he enjoys so much at Cheshire Academy. His efforts did not […]
WTNH News 8 Spotlights Cheshire Academy Linebacker Vince Reno ’27
Star Senior Talked About College Prospects, Growing Up in a Football Family Vince Reno ’27, the youngest of a family of football standouts, talked about his prospects for college play and what it’s like to be the son of former Yale University head coach Tony Reno and brother of Yale’s current quarterback, Dante, in an interview with WTNH News 8. “I grew up with it,” […]
Hearst Media Spotlights Cheshire Academy’s Approach to Language Learning
Connecticut’s largest media chain explores how language develops the brain and global citizenship Cheshire Academy’s comprehensive approach to language learning took center stage in a Hearst CT Media Group feature story that ran in the Connecticut Post, Greenwich Time, Stamford Advocate, and several other state newspapers. At CA, students from around the globe are discovering that learning a language is about far more than words—it’s about becoming a different kind of thinker, and a different kind of citizen. […]
‘They Believed in Me Before I Did:’ Cheshire Academy’s Class of 2026 Marks a Milestone Commencement
An alum returns as keynote speaker, a new tradition takes root, and 111 graduates carry CA’s lessons forward Cheshire Academy held its historic 232nd annual Commencement Exercises June 6 in a festive celebration of chances taken and given and the school’s faith in each student’s burgeoning potential. Under sunny skies and a warm wind, the […]
